Chronic lower leg pain results from various conditions, most commonly, medial tibial stress syndrome, stress fracture, chronic exertional compartment syndrome, nerve entrapment, and popliteal artery entrapment syndrome. Symptoms associated with these conditions often overlap, making a definitive diagnosis difficult. As a result, an algorithmic approach was created to aid in the evaluation of patients with complaints of lower leg pain and to assist in defining a diagnosis by providing recommended diagnostic studies for each condition. A comprehensive physical examination is imperative to confirm a diagnosis and should begin with an inquiry regarding the location and onset of the patient's pain and tenderness. Confirmation of the diagnosis requires performing the appropriate diagnostic studies, including radiographs, bone scans, magnetic resonance imaging, magnetic resonance angiography, compartmental pressure measurements, and arteriograms. Although most conditions causing lower leg pain are treated successfully with nonsurgical management, some syndromes, such as popliteal artery entrapment syndrome, may require surgical intervention. Regardless of the form of treatment, return to activity must be gradual and individualized for each patient to prevent future athletic injury.